urethane

General Material Information

Preferred name	urethane
Trivial Name	Carbamic acid, ethyl ester
Short Description	ethyl ester of carbamic acid
Formula	C3 H7 N O2
CAS Number	51-79-6
Deleted CAS Number	121382-27-2
ECHA Number	200-123-1
FDA UNII	3IN71E75Z5
Nikkaji Number	J2.306J
MDL	MFCD00007966
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	ethyl ester of carbamic acid carbamate, ethyl carbamic acid ethyl ester carbamic acid, ethyl ester (8CI 9CI) ethyl aminoformate ethyl carbamate ethyl ester of carbamic acid ethyl hydrogen carbonimidate ethyl urethane ethylcarbamate ethylurethane leucethane leucethanem leucothane methanol, 1-ethoxy-1-imino- o-ethyl carbamate o-ethylurethane pracarbamin pracarbamine urethane [INN:BAN:DCF] [INN] Carbamic acid, ethyl ester NSC 746 Urethan MeSH ID: D014520

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Literature & References

	ethyl carbamate
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	51-79-6
Pubchem (cid):	5641
Pubchem (sid):	134972752

Publications by PubMed
A survey of levels of ethyl carbamate in alcoholic beverages in 2009-2012, Hebei Province, China.
Validation (in-house and collaboratory) of the quantification method for ethyl carbamate in alcoholic beverages and soy sauce by GC-MS.
Ultrasound-assisted emulsification-microextraction for the sensitive determination of ethyl carbamate in alcoholic beverages.
Determination of ethyl carbamate in wine by high performance liquid chromatography.
Nesfatin-1 induces Fos expression and elicits dipsogenic responses in subfornical organ.
Isolation and characterization of urethanase from Penicillium variabile and its application to reduce ethyl carbamate contamination in Chinese rice wine.
Determination of ethyl carbamate in cachaça produced from copper stills by HPLC.
A comparative study of the modulatory effects of (-)-cubebin on the mutagenicity/recombinogenicity induced by different chemical agents.
Galanin-like peptide (GALP) facilitates thermogenesis via synthesis of prostaglandin E2 by astrocytes in the periventricular zone of the third ventricle.
[Direct determination of ethyl carbamate in Chinese rice wine and grape wine by ultra performance liquid chromatography-electrospray ionization tandem mass spectrometry].
A micro-flow-batch analyzer with solenoid micro-pumps for the photometric determination of iodate in table salt.
Chemopreventive effects of pterostilbene on urethane-induced lung carcinogenesis in mice via the inhibition of EGFR-mediated pathways and the induction of apoptosis and autophagy.
Interactions of sulforaphane and dimethyl sulfoxide with methyl methanesulfonate, urethane, 4-nitroquinoline-1-oxide and hydrogen peroxide in the Drosophila melanogaster wing spot test.
Reduction in the number of animals and the evaluation period for the positive control group in Tg.rasH2 short-term carcinogenicity studies.
A sutureless aortic stent-graft based on a nitinol scaffold bonded to a compliant nanocomposite polymer is durable for 10 years in a simulated in vitro model.
Nesfatin-1 inhibits gastric acid secretion via a central vagal mechanism in rats.
Multiple headspace solid-phase microextraction using a new fiber for avoiding matrix interferences in the quantitative determination of ethyl carbamate in pickles.
Beetroot red (betanin) inhibits vinyl carbamate- and benzo(a)pyrene-induced lung tumorigenesis through apoptosis.
Biogenic amines and ethyl carbamate in primitivo wine: survey of their concentrations in commercial products and relationship with the use of malolactic starter.
Derivatization followed by gas chromatography-mass spectrometry for quantification of ethyl carbamate in alcoholic beverages.
Antibacterial activity of reactive quaternary ammonium compounds in solution and in nonleachable coatings.
[Multiple headspace solid-phase microextraction after matrix modification for the determination of ethyl carbamate in alcoholic beverages using gas chromatography].
Multiple headspace solid-phase microextraction after matrix modification for avoiding matrix effect in the determination of ethyl carbamate in bread.
[Survey and analysis of ethyl carbamate in commercial fermented foods in Hangzhou in 2010].
Wine features related to safety and consumer health: an integrated perspective.
Multiple headspace solid-phase microextraction of ethyl carbamate from different alcoholic beverages employing drying agent based matrix modification.
Nesfatin-1 stimulates renal sympathetic nerve activity in rats.
Effects of cyclophosphamide on the kaolin consumption (pica behavior) in five strains of adult male rats.
Theta phase classification of interneurons in the hippocampal formation of freely moving rats.
Is contaminated unrecorded alcohol a health problem in the European Union? A review of existing and methodological outline for future studies.
The concentration of ethyl carbamate in commercial ume (Prunus mume) liqueur products and a method of reducing it.
The protective effects of Curcuma longa Linn. extract on carbon tetrachloride-induced hepatotoxicity in rats via upregulation of Nrf2.
The composition of unrecorded alcohol from eastern Ukraine: is there a toxicological concern beyond ethanol alone?
Effects of Eucommia leaf extracts on autonomic nerves, body temperature, lipolysis, food intake, and body weight.
Functional enhancement of Sake yeast strains to minimize the production of ethyl carbamate in Sake wine.
Responses to cholecystokinin in the ventromedial nucleus of the rat hypothalamus in vivo.
Effect of an intraduodenal injection of fat on the activities of the adrenal efferent sympathetic nerve and the gastric efferent parasympathetic nerve in urethane-anesthetized rats.
Application of the margin of exposure (MoE) approach to substances in food that are genotoxic and carcinogenic: example: ethyl carbamate (CAS 51-79-6).
Genotoxicity studies of organically grown broccoli (Brassica oleracea var. italica) and its interactions with urethane, methyl methanesulfonate and 4-nitroquinoline-1-oxide genotoxicity in the wing spot test of Drosophila melanogaster.
Association between quality of cheap and unrecorded alcohol products and public health consequences in Poland.
Ethyl carbamate in alcoholic beverages from Mexico (tequila, mezcal, bacanora, sotol) and Guatemala (cuxa): market survey and risk assessment.
Silicone-urethane adhesive for improved coverslip mounting and leak-free preparation of living cell observation chambers.
Detection of arc genes related with the ethyl carbamate precursors in wine lactic acid bacteria.
Findings of P300-like and CNV-like potentials in rat model of depression following repeatedly forced swim stress.
Risk of human health by particulate matter as a source of air pollution--comparison with tobacco smoking.
Centrally administered neuromedin U elevates plasma adrenaline by brain prostanoid TP receptor-mediated mechanisms in rats.
Spectrophotometric determination of urea in sugar cane distilled spirits.
Cardioactive and vasoactive effects of natural wild honey against cardiac malperformance induced by hyperadrenergic activity.
Original normal-phase high-performance liquid chromatographic separation of monoacylglycerol classes from extra virgin olive oil triacylglycerols for their stereospecific analysis.
Preproghrelin-derived peptide, obestatin, fails to influence food intake in lean or obese rodents.
Automatic regulation of occlusal force because of hardness-change of the bite object.
Effect of esophageal distention on basal and stimulated gastric acid secretion in rats.
Comparative genotoxicity evaluation of imidazolinone herbicides in somatic cells of Drosophila melanogaster.
Esthetic brackets: the influence of filler level on color stability.
Amorphous calcium phosphate/urethane methacrylate resin composites. I. Physicochemical characterization.
Safety evaluation of certain contaminants in food. Prepared by the Sixty-fourth meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA).
Survey of ethyl carbamate in fermented foods sold in the United Kingdom in 2004.
Alpha-lactalbumin suppresses interleukin-6 release after intestinal ischemia/reperfusion via nitric oxide in rats.
Oxidation of vinyl carbamate and formation of 1,N6-ethenodeoxyadenosine in murine lung.
HPLC separation and NMR structural elucidation of sn-1,2-, 2,3-, and 1,3-diacylglycerols from olive oil as naphthylethylurethane derivatives.
Critical parameter of burst pressure measurement in development of bypass grafts is highly dependent on methodology used.
Comparison of methods for extraction of ethyl carbamate from alcoholic beverages in gas chromatography/mass spectrometry analysis.
Effect of different Thai traditional processing of various hot chili peppers on urethane-induced somatic mutation and recombination in Drosophila melanogaster: assessment of the role of glutathione transferase activity.
Neuroprotective effects of resveratrol on cerebral ischemia-induced neuron loss mediated by free radical scavenging and cerebral blood flow elevation.
Final report of the safety assessment of niacinamide and niacin.
Bacteria important during winemaking.
Retrospective trends and current status of ethyl carbamate in German stone-fruit spirits.
Application of positive ion chemical ionisation and tandem mass spectrometry combined with gas chromatography to the trace level analysis of ethyl carbamate in bread.
Rapid screening for ethyl carbamate in stone-fruit spirits using FTIR spectroscopy and chemometrics.
Mechanisms involved in A/J mouse lung tumorigenesis induced by inhalation of an environmental tobacco smoke surrogate.
Effects of storage time and temperature on the concentration of ethyl carbamate and its precursors in wine.
Application of tandem mass spectrometry combined with gas chromatography to the routine analysis of ethyl carbamate in stone-fruit spirits.
Effect of ethanol on the tumorigenicity of urethane (ethyl carbamate) in B6C3F1 mice.
Orexin-A (Hypocretin-1) and leptin enhance LTP in the dentate gyrus of rats in vivo.
Cholecystokinin and prostaglandins inhibit responses of vagal afferent activity to systemic administration of nicotine in anesthetized rats.
[An extended evaluation of a neuroleptanesthesia for the guinea pig with analysis of mixed expiratory gases during spontaneous breathing. Effects of fasting on the cardiorespiratory system and metabolism].
Acute inhibition of the hypothalamic paraventricular nucleus decreases renal sympathetic nerve activity and arterial blood pressure in water-deprived rats.
[Effects of the spaceflight on organ-development in the neonatal rats: results in the Neurolab (STS-90)].
Orexin-A-sensitive site for energy expenditure localized in the arcuate nucleus of the hypothalamus.
Antimutagenic properties of bell and black peppers.
Analysis of ethyl carbamate in wines using solid-phase extraction and multidimensional gas chromatography/mass spectrometry.
Gastric acid secretion stimulated by centrally injected nociceptin in urethane-anesthetized rats.
Citrulline as the main precursor of ethyl carbamate in model fortified wines inoculated with Lactobacillus hilgardii: a marker of the levels in a spoiled fortified wine.
Action of CCK and 5-HT on lateral hypothalamic neurons depends on early postnatal nutrition.
Hippocampal synaptic plasticity is modulated by theta rhythm in the fascia dentata of adult and aged freely behaving rats.
Energy expenditure by intracerebroventricular administration of orexin to anesthetized rats.
Inhibition of genotoxicity by saffron (Crocus sativus L.) in mice.
An improved method for determination of ethyl carbamate in Korean traditional rice wine.
Thermogenesis induced by intravenous infusion of hypertonic solutions in the rat.
Effect of acute and subchronic subcutaneous urocortin on blood pressure and food consumption in ob/ob mice.
Copper(II) catalysis in cyanide conversion into ethyl carbamate in spirits and relevant reactions.
Anti-genotoxicity of trans-anethole and eugenol in mice.
Ghrelin acts in the central nervous system to stimulate gastric acid secretion.
Quantification of etheno-DNA adducts using liquid chromatography, on-line sample processing, and electrospray tandem mass spectrometry.
Vitamin E inhibits cell proliferation and the activation of extracellular signal-regulated kinase during the promotion phase of lung tumorigenesis irrespective of antioxidative effect.
Determination of ethyl carbamate in some fermented Korean foods and beverages.
Susceptibility of nonhuman primates to carcinogens of human relevance.
Effect of resin matrix ratio, storage medium, and time upon the physical properties of a radiopaque dental composite.
Three body wear studies of five dental composites preconditioned in food simulating media.
Anti-genotoxicity and glutathione S-transferase activity in mice pretreated with caffeinated and decaffeinated coffee.
Activation of extracellular signal-regulated kinase in lung tissues of mice treated with carcinogen.
Locus coeruleus-mediated inhibition of chemosensory responses in the rat nucleus tractus solitarius is mediated by alpha2-adrenoreceptors.
A physiologically based pharmacokinetic model for 2,4-toluenediamine leached from polyurethane foam-covered breast implants.
The modulation effect of vitamin E on prostaglandin E2 level and ornithine decarboxylase activity at the promotion phase of lung tumorigenesis in mice.
Genotoxicity of ethyl carbamate (urethane) in Salmonella, yeast and human lymphoblastoid cells.
The inhibitory effect of vitamin E on K-ras mutation at an early stage of lung carcinogenesis in mice.
The contribution of azodicarbonamide to ethyl carbamate formation in bread and beer.
The effect of azodicarbonamide concentrations on ethyl carbamate concentrations in bread and toast.
Ethyl carbamate levels resulting from azodicarbonamide use in bread.
Effects of diabetes and food deprivation on shivering activity during progressive hypothermia in the rat.
NTP technical report on toxicity studies of urethane in drinking water and urethane in 5% ethanol administered to F344/N rats and B6C3F1 mice.
Formation of etheno and oxoethyl adducts in liver DNA from rats exposed subchronically to urethane in drinking water and ethanol.
Anti-genotoxic effects in mice after the interaction between coffee and dietary constituents.
Protection by coffee against somatic genotoxicity in Drosophila: role of bioactivation capacity.
Peptide YY release after intraduodenal, intraileal, and intracolonic administration of nutrients in rats.
Genotoxicity of agaritine in the lacI transgenic mouse mutation assay: evaluation of the health risk of mushroom consumption.
Cardiovascular effects of tropacocaine in conscious and anesthetized rabbits: lack of evidence for neuro-cardiac interactions and acute neurotoxicity.
The area under the plasma concentration curve (AUC) of urethane in mice and the influence of concomitant administration of ethanol.
Determination of ethyl carbamate in alcoholic beverages and soy sauce by gas chromatography with mass selective detection: collaborative study.
Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes.
Indentation cracking of composite matrix materials.
Health risks for women with breast implants.
Changes in properties of neuronal responses in two cortical taste areas in rats of various ages.
Investigation of the presence of biogenic amines and ethyl carbamate in kenkey made with maize and maize-cowpea mixtures as influenced by process conditions.
Tumor incidence in a chemical carcinogenesis study of nonhuman primates.
Altered maternal zinc metabolism following exposure to diverse developmental toxicants.
Induction of DNA damage by urethane in mouse testes: DNA binding and unscheduled DNA synthesis.
A survey of ethyl carbamate in beverages, bread and acidified milks sold in Denmark.
Isolation of bilobalide and ginkgolide A from Ginkgo biloba L. shorten the sleeping time induced in mice by anesthetics.
A method for the determination of methyl carbamate and ethyl carbamate in wines.
Degradation of five polyurethane gastric bubbles following in vivo use: SEC, ATR-IR and DSC studies.
The role of metallothionein induction and altered zinc status in maternally mediated developmental toxicity: comparison of the effects of urethane and styrene in rats.
Inhibition by wine of tumorigenesis induced by ethyl carbamate (urethane) in mice.
Ethyl carbamate: analytical methodology, occurrence, formation, biological activity and risk assessment.
Genetic engineering of a sake yeast producing no urea by successive disruption of arginase gene.
Effects of cholecystokinin (CCK-8) on two classes of gastroduodenal vagal afferent fibre.
Ethyl carbamate (urethane) in alcoholic beverages and foods: a review.
[A role of periodontal afferents in the control of jaw-closing muscle activities].
Ethyl carbamate metabolism: in vivo inhibitors and in vitro enzymatic systems.
The in vivo erythrocyte micronucleus test: measurement at steady state increases assay efficiency and permits integration with toxicity studies.
Ambient temperature modulation of fenfluramine-induced thermogenesis in the rat.
The carcinogenic potential of ethyl carbamate (urethane): risk assessment at human dietary exposure levels.
Mutagenicity, metabolism, and DNA interactions of urethane.
Carcinogenesis of foods.
Chronic ethanol intake and reduction of lung tumours from urethane in strain A mice.
Developmental toxicity of urethan.
Ethyl carbamate levels in selected fermented foods and beverages.
Investigation of ethyl carbamate levels in some fermented foods and alcoholic beverages.
Influence of food-simulating solvents on resin composites and glass-ionomer restorative cement.
Induction of hepatocellular carcinoma in nonhuman primates by chemical carcinogens.
Contamination of alcoholic products by trace quantities of ethyl carbamate (urethane).
Application of gas chromatography/matrix isolation/Fourier transform infrared spectrometry to the determination of ethyl carbamate in alcoholic beverages and foods.
Rapid gas chromatographic method for determining ethyl carbamate in alcoholic beverages with thermal energy analyzer detection.
Effect of capsaicin pretreatment on capsaicin-induced catecholamine secretion from the adrenal medulla in rats.
Agonist and antagonist activities at benzodiazepine receptors of a novel series of quinoline derivatives.
Gas chromatographic-mass spectrometric determination of ethyl carbamate in alcoholic beverages.
Inhibition of the localization of urethane in mouse tissues by ethanol.
A simple gas chromatography method for the determination of ethylcarbamate in spirits.
Carotid sinus reflexes in rats given small doses of lead.
The study of mutagenic activity of carcinogens and other chemical agents with Salmonella typhimurium assays: testing of 126 compounds.
Response of the cardiovascular system to catecholamines in rats given small doses of lead.
NTP Toxicology and Carcinogenesis Studies of Dichloromethane (Methylene Chloride) (CAS No. 75-09-2) in F344/N Rats and B6C3F1 Mice (Inhalation Studies).
The regulatory control to toxic chemicals in food.
[Mutagenic activity of carcinogens and other chemical agents in Salmonella typhimurium tests].
Effects of small amygdaloid lesions on pancreatic exocrine secretion.
Pharmacologic and genetic studies on the modulatory effects of butylated hydroxytoluene on mouse lung adenoma formation.
Decreased chronotropic responses to adrenergic stimulation following sinoaortic denervation in the rat.
Effect of the plant growth regulator, 2-chloroethylphosphonic acid, on spontaneous and chemically-induced lung tumorigenesis in strain A mice.
Loss of tissue sensitivity to growth hormone during maternal deprivation in rats.
[Studies on growth hormone secretion in starved rats under urethane anesthesia (author's transl)].
Hypothalamic unit responses to alimentary perfusions in the anesthetised rat.
On the amounts of urethane formed in diethyl pyrocarbonate treated beverages.
Chromosome tests with 134 compounds on Chinese hamster cells in vitro--a screening for chemical carcinogens.
Xenobiotics and molecular teratology.
Environmental factors in the origin of cancer and estimation of the possible hazard to man.
[Effect of brain stem lesions on hibernation of the hamster (Cricetus cricetus L.)].
Gas chromatographic analysis of urethan (ethyl carbamate) in wine.
Test for carcinogenicity of food additives and chemotherapeutic agents by the pulmonary tumor response in strain A mice.
Organotin compounds: industrial applications and biological investigation.
Long-term toxicity studies of chlorpropham and propham in mice and hamsters.
Diethyl pyrocarbonate: formation of urethan in treated beverages.
Further chapters in the hydrazine story.
More about isonicotinic acid hydrazide toxicity.
Organ culture of lung tissue as a method for studying lung tumours and blastomogenic action of substances that can induce them.
Use of newborn and infant animals in carcinogenicity testing.

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Formulations/Preparations: grades: technical; nf.

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Sigma-Aldrich

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	89.094192504883
Vapor Pressure	0.7 mmHg @ 25 °C
Flash Point TCC Value	92.22 °C TCC
logP (o/w)	-0.15
Solubility
water, 4.80E+05 mg/L @ 15 °C (exp)	Yes
water, 1.68e+005 mg/L @ 25 °C (est)	Yes

Safety Information

Safety information


Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-chicken LDLo 2188 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. intraarterial-guinea pig LDLo 800 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928. intravenous-guinea pig LDLo 800 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928. intraperitoneal-mouse LD50 1539 mg/kg Progress in Mutation Research. Vol. 1, Pg. 682, 1981. intravenous-mouse LD50 500 mg/kg Acta Pharmaceutica Jugoslavica. Vol. 5, Pg. 43, 1955. oral-mouse LD50 2500 mg/kg Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 595, 1959. unreported-mouse LD50 2000 mg/kg British Journal of Cancer. Vol. 6, Pg. 160, 1952. parenteral-mouse LDLo 1000 mg/kg GASTROINTESTINAL: PERITONITIS Progress Report for Contract No. PH-43-63-1132, Submitted to the National Cancer Institute by Scientific Associates, Inc. Vol. PH-43-62-483 intravenous-rabbit LDLo 2000 mg/kg "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 272, 1973. intramuscular-rat LD50 1400 mg/kg Zeitschrift fuer Krebsforschung und Klinische Onkologie. Vol. 84, Pg. 227, 1975. intraperitoneal-rat LD50 1500 mg/kg Cancer Research. Vol. 26, Pg. 1448, 1966. oral-rat LD50 1809 mg/kg Cancer Letters Vol. 57, Pg. 37, 1991.
Dermal Toxicity:
subcutaneous-mouse LD50 1750 mg/kg Gann. Japanese Journal of Cancer Research. Vol. 63, Pg. 731, 1972. subcutaneous-rat LDLo 1800 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 182, Pg. 348, 1936.
Inhalation Toxicity:
Not determined

Safety in use information

Category:
information only not used for fragrances or flavors
Recommendation for urethane usage levels up to:
	not for fragrance use.

Recommendation for urethane flavor usage levels up to:
	not for flavor use.